Process for producing nitrogen-containing compounds

Abstract

The present invention relates to a process for producing an aliphatic amine, comprising the step of contacting a linear or branched, or cyclic aliphatic alcohol having 6 to 22 carbon atoms with ammonia and hydrogen in the presence of a catalyst formed by supporting at least (A) a ruthenium component produced by hydrolysis of a ruthenium compound on a carrier, or by further supporting, in addition to the component (A), a specific second metal component or a specific third metal component on the carrier. According to the process of the present invention, an aliphatic primary amine can be produced from an aliphatic alcohol with a high catalytic activity and a high selectivity.

1. A process for producing an aliphatic amine, comprising contacting a linear or branched, or cyclic aliphatic alcohol having 6 to 22 carbon atoms with ammonia and hydrogen in the presence of a catalyst that comprises, present on a carrier, (A) a ruthenium component produced by hydrolysis of a ruthenium compound. 
     
     
       2. The process according to  claim 1 , wherein the catalyst further comprises, present on the carrier, (B) at least one metal component selected from the group consisting of nickel, cobalt and tungsten, which is produced by hydrolysis of a compound of at least one metal selected from the group consisting of nickel, cobalt and tungsten. 
     
     
       3. The process according to  claim 1 , wherein the catalyst further comprises, present on the carrier, (B) at least one metal component selected from the group consisting of nickel and cobalt which is produced by hydrolysis of at least one of a nickel compound and a cobalt compound, and (C) at least one metal component selected from the group consisting of lanthanum, yttrium, magnesium and barium, which is produced by hydrolysis of at least one of a lanthanum compound, a yttrium compound, a magnesium compound and a barium compound. 
     
     
       4. The process according to  claim 3 , wherein a content of the at least one metal component (C) selected from the group consisting of lanthanum, yttrium, magnesium and barium in the catalyst is from 0.01 to 10% by mass in terms of the metal element on the basis of a total amount of the catalyst. 
     
     
       5. The process according to  claim 1 , wherein the carrier comprises at least one compound selected from the group consisting of a high molecular weight compound, a metal phosphate, and a porous oxide. 
     
     
       6. The process according to  claim 1 , wherein the carrier comprises a porous oxide. 
     
     
       7. The process according to  claim 1 , wherein the carrier comprises a porous oxide that is at least one oxide selected from the group consisting of alumina, zirconia, titania and an aluminosilicate diatomaceous earth, a hydrotalcite compound, an alkali earth metal oxide, and niobia. 
     
     
       8. The process according to  claim 2 , wherein a content of the component (B) in the catalyst is from 0.1 to 25% by mass in terms of the metal element on the basis of a total amount of the catalyst. 
     
     
       9. The process according to  claim 1 , wherein a content of the ruthenium component (A) in the catalyst is from 0.1 to 25% by mass in terms of metallic ruthenium on the basis of a total amount of the catalyst. 
     
     
       10. The process according to  claim 1 , wherein the catalyst is dried after said hydrolysis at a temperature of 140° C. or lower. 
     
     
       11. The process according to  claim 1 , wherein the catalyst is reduced after said hydrolysis in the presence of at least one reducing agent selected from the group consisting of formaldehyde, hydrazine and sodium borohydride. 
     
     
       12. The process according to  claim 1 , wherein said contacting is carried out at a temperature of 120 to 280° C. 
     
     
       13. The process according to  claim 1 , wherein said contacting is carried out under such a condition that a molar ratio of ammonia to the aliphatic alcohol (ammonia/aliphatic alcohol) is from 0.5 to 10. 
     
     
       14. The process according to  claim 1 , wherein the catalyst is present in an amount of 0.1 to 20% by mass on the basis of the aliphatic alcohol. 
     
     
       15. The process according to  claim 1 , wherein the aliphatic amine comprises an aliphatic primary amine. 
     
     
       16. The process according to  claim 3 , wherein a content of the component (B) in the catalyst is from 0.1 to 25% by mass in terms of the metal element on the basis of a total amount of the catalyst.